Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinol­ines

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• 作者：Ashwini Borah and Pranjal Gogoi
• 关键词：Synthetic methods ; Domino reactions ; Palladium ; C&ndash ; C coupling ; Nitrogen heterocycles
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：2016
• 期：12
• 页码：2200-2206
• 全文大小：1077K
• ISSN：1099-0690

文摘

A Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro ,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon–carbon and carbon–nitrogen bond formation in a single reaction vessel. The requisite β-chloro ,β-unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)₂ is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram-scale synthesis of a trispheridine alkaloid.